I Was Making Money But Still Failing. Here’s Why - Pt 2

After the Universal Pizza experience, I stopped pitching dreams and started building small experiments. What I didn't know yet was that I was about to discover two things that would shape everything, digital leverage and the power of solving real problems.

My first taste of digital leverage

Not long after, a friend offered me space on his server. I built a simple hosting website so sold shared server space of my own, and to my surprise, two strangers actually signed up. All I had to do was keep paying my friend monthly and pocket the difference. It wasn't much, barely enough to notice, but it was the first time I'd made money from something digital that didn't require constant work.

A small setup could generate income in the background. That was a different kind of freedom. But there was a fatal flaw I didn't see yet. I didn't own the infrastructure. Everything depended on my friend's server staying alive, and eventually it didn't. He ran out of money and couldn't maintain it. The business just stopped. All those customers, all that passive income (emphasis on past tense), gone overnight because I had no control over the foundation it was built on.

Building a business on someone else's server is like building a house on rented land. When they stop paying the rent, your house disappears too.

It was also a ceiling. Two customers weren't going to grow into a living anyway. But the real lesson was harder. You can build on someone else's ground, but only if they're stable. Make sure they can stay in business. My friend couldn't maintain the server, so the whole thing fell apart. I'd proven the concept, but I needed something I actually owned and something that scaled differently, something that didn't just earn passively but could earn actively too.

Reward Charts and Real Problems

A few years later, I wanted to help my son build a routine in a way that felt fun rather than forced. I designed a reward chart with stars he could stick on every day, and he loved it. Other parents saw it and asked if I could make one for their kids too.

I printed a few copies and posted them online. Then a few more. Then suddenly people were ordering faster than I could print. Parents wanted them personalised with their child's name. They wanted different themes. They wanted sets for different routines, one for morning, one for bedtime, one for homework.

My kitchen became a print shop. My living room became a laminating factory. Professional business operations, right next to where I made dinner.

Before long, I was earning about $900 NZD a week from my kitchen table with a printer. For roughly 9 hours of work a week, I was making what would be equivalent to earning $170 per hour in today's dollars. At 22 years old, unemployable by everyone else's standards (enthusiasm apparently not being a marketable skill), I made more than any job would have paid me, all while raising young children. It felt like proof that I wasn't broken, just different.

And all of this started with a $200 computer, a $120 printer, and a laminator worth maybe $90. Less than $500 in total startup costs. That was the entire business.

But I didn't stop at just selling. I obsessed over optimisation. I upgraded to a better printer, negotiated bulk deals with local suppliers (they were solo operators too, so we understood each other), and started ordering ink from overseas to cut costs. I bought an industrial-grade laminator and sourced cheaper supplies through business contacts. Every cost I shaved off meant higher profit margins. Every efficiency I squeezed out meant more time with my kids instead of at the printer. I was winning, but racing against my own limits. There were only so many hours in a day, only so much I could produce myself.

That was my first real success. I had taught myself Photoshop and learned that good design was less about decoration and more about clarity and structure. That lesson shaped everything I'd build later, including how I'd eventually approach interface design and writing code.

Then suddenly I got pulled off the platform I was selling on. I thought fan art was an acceptable thing to sell online. People on DeviantArt did it all the time. But on this platform, it absolutely wasn't. Years of work, gone because I didn't read the terms properly. 'I'm sure it's fine' held up about as well as you'd expect in a legal dispute.

Freelancing pays

Once I knew I could design, I began building websites for other people. My first client paid two hundred dollars, which felt like a fortune after making nothing again. I didn't know what to charge or how to manage expectations, but it taught me something crucial. My time and skill had value.

Each project paid better than the last. But I was still trading time for money, still capped by the hours I could work.

Perfume spritzers and breaking things down

After reward charts, I tried something different. I bought full bottles of perfume wholesale for about $50 each, then split them into five millilitre spritzers and sold them for $7 each. A single bottle could return around $150. Perfume middleman, operating out of my kitchen. Living the dream no kid ever had.

The perfume business worked well. But I was back to the same problem. I was limited by my own capacity. I could only split so many bottles, only list so many items. I was growing, but I was also overwhelmed.

This was the same logic I'd used with hosting, take something large, divide it into smaller, more accessible pieces. But I needed something different. I needed to divide my time into smaller, more accessible pieces.

The pattern emerging

Looking back now, I can see what I couldn't see then. Every business taught me something valuable. Hosting showed me passive income was possible. Reward charts proved that solving real problems creates demand. Freelancing taught me my skills had worth. Perfume spritzers reinforced the power of making things more accessible.

But they all hit the same ceiling. My own capacity. My own time. My own hands. I was both the boss and the problem.

I was about to discover the solution to that problem. And it would change everything.

Lesson: You can build profitable businesses solving real problems, but if you're trading hours for dollars, you'll always hit a ceiling. The next step is finding leverage.